CN1209313A - 可光致阳离子固化的组合物及其用途 - Google Patents
可光致阳离子固化的组合物及其用途 Download PDFInfo
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/20—Protective coatings for natural or artificial teeth, e.g. sealings, dye coatings or varnish
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/30—Compositions for temporarily or permanently fixing teeth or palates, e.g. primers for dental adhesives
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/80—Preparations for artificial teeth, for filling teeth or for capping teeth
- A61K6/884—Preparations for artificial teeth, for filling teeth or for capping teeth comprising natural or synthetic resins
- A61K6/891—Compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
- C08G65/06—Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
- C08G65/16—Cyclic ethers having four or more ring atoms
- C08G65/18—Oxetanes
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
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- Health & Medical Sciences (AREA)
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- Oral & Maxillofacial Surgery (AREA)
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- General Health & Medical Sciences (AREA)
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Abstract
本发明涉及用可见光可阳离子固化的组合物,该组合物含有:(a)0.01—8wt.%的至少一种二芳基碘鎓化合物,(b)0.01—8wt.%的至少一种α-二羰基化合物,(c)10.0—99.9wt.%的至少一种含环氧基和/或氧杂环丁烷基的化合物,(d)0—85wt.%的改性剂,如填料、染料、颜料、流动改进剂、触变剂、聚合增稠剂、具有氧化作用的添加剂、稳定剂和阻聚剂,其特征在于组合物还含有(e)0.001—5wt.%的至少一种芳族胺。该组合物具有浅的固有色,固化时气味小,而且固化后产生了具有优异机械性能的组合物。
Description
本发明涉及基于环氧树脂和/或氧杂环丁烷的组合物,该组合物在用可见光照射期间或之后通过阳离子聚合而固化。详细地讲,本发明涉及仅具有浅的固有色的组合物及其在牙齿制剂中的用途。
正如人们公知的,包括含有环氧基和/或氧杂环丁烷基团的化合物的组合物可以阳离子固化。阳离子聚合通常由路易斯酸或布朗斯台德酸引发,这些酸可以被加入到可阳离子固化的配料中,或者通过在先的化学反应、尤其是光化学反应产生。
许多通常所说的光引发剂,即在波长范围为215-400nm的光的作用下分解以形成布朗斯台德酸的光引发剂公知可用于含有环氧基的组合物中。这些引发剂包括如重氮化合物(US-A-3205157)、锍化合物(US-A-4173476)和碘鎓化合物(US-A-4264703,US-A-4394403)。但是,就可阳离子固化的组合物的聚合而言,上述例子有必要使用紫外光。
同样公知的是对光不稳定的物质,该物质在用可见光照射时释放出路易斯酸和布朗斯台德酸,并且能够引起可阳离子固化的配料的聚合。这些光引发剂一般是环戊二烯基-铁-芳烃配合物的衍生物(EP-A-0094915,WO96/03453,EP-A-0661324)。这些光引发剂的缺点是产生褐色至黑色的聚合物,这点在补牙应用中导致美学上令人不满意的结果。此外,固化过程中产生了强烈的异丙基苯气味,这点不是补牙应用中所希望的。
同样公知的是在可见光范围内使阳离子聚合成为可能的引发剂体系。但是,这些体系包括有色的敏化剂如呫吨或芴,它们的发色团残留下来并使聚合物着色(WO-95/14716;化学文摘,vol.121,1994,ref.58043z),因此不适用于美学上可接受的补牙组合物。
WO96/13538公开了环氧化物体系,该体系可以在可见光中固化,并且具有改进的硬化深度,它包括:a)可阳离子聚合的环氧树脂,b)含羟基的材料,c)芳基碘鎓盐,和d)α-二羰基化合物。α-二羰基化合物在可见光范围内起敏化剂作用,特别优选采用樟脑醌。正如人们公知的,樟脑醌在用可见光照射时分解产生自由基,长期以来该反应被用来引发含双键配料、最好是牙齿制剂的固化。
另外公知的是樟脑醌与碘鎓化合物的混合引发剂体系,但是它们仅被用于含双键的或其它通过自由基固化的组合物的聚合,或者被用于混杂的单体混合物的聚合(US-A-5554676,US-A-4828583)。
尽管从许多出版物中得知,在环氧化物阳离子聚合(用碘鎓化合物引发,据说已得到增柔的环氧化物组合物)中,使用含羟基的化合物使反应加快(US-A-4256828;US-A-4231951;EP-B-0119425;DE-A-4324322.3),但是使用较高浓度(如WO96/13538的实施例1-6、10-16、22、23、32和33中所述)含羟基的低分子量化合物会导致结合入聚合网络不完全,其结果是不良的机械性能和高的可提取量。
本发明的目的是提供可光致阳离子固化的组合物,该组合物具有浅的固有色,固化时气味小,而且固化后产生了具有优异的机械性能(如高附着力、高抗压强度及抗弯强度)和低的可提取量的组合物。
该目的由可光致阳离子固化的组合物达到,该组合物含有:a)0.01-8wt.%、优选0.1-5wt.%的至少一种二芳基碘鎓化合物或二芳基碘鎓化合物的混合物,b)0.01-8wt.%、优选0.1-5wt.%的至少一种α-二羰基化合物,c)10.0-99.9wt.%的至少一种含环氧基和/或氧杂环丁烷基的化合物,d)0-85wt%的改性剂,如填料、染料、颜料、流动改进剂、触变剂、聚合增稠剂、具有氧化作用的添加剂、稳定剂和阻聚剂,其特征在于还含有e)0.001-5wt.%、优选0.01-3wt.%的至少一种芳族胺。
意外的是用作成分e)的胺对光致阳离子聚合有促进作用。现有技术中(DE-A-19534594,WO96/13538)是这样阐述的:胺对聚合具有阻滞作用或甚至具有抑制作用。另外,完全意外的是在正在聚合的组合物中,少的添加量如0.001wt.%已经具有促进作用。
成分a)的二芳基碘鎓化合物具有以下结构:
[((R1)aAr1)-I-(Ar2(R2)b)]+Y-Ar1和Ar2互相独立地可为不同的取代或未取代的、稠合或非稠合的具有4-20个C原子的芳族体系,例如苯基、甲苯基、枯基、茴香基、氯苯基、硝基苯基、萘基、噻吩基、呋喃基和吡唑基,其中R1和R2相同或不同,并且互相独立地代表H原子、具有1-19个、优选1-9个C原子的脂族基,其中的一个或多个C原子可以用O、C=O、-O(C=O)-、F、Cl、Br、SiR3 3和/或NR3 2代替,其中R3是具有1-7个C原子的脂族基,其中的一个或多个C原子可以用O、C=O和/或-O(C=O)-代替,a和b互相独立地可为1-5。芳族体系Ar1和Ar2可以通过R1和/或R2互相连接。
阴离子Y-是具有以下结构的低亲核性阴离子:
KxLy -其中K是第Ⅲ、Ⅴ或Ⅶ主族的元素,例如B、Al、P、Sb、As或I,x可设定为1-4的数值,L互相独立地代表具有1-25个C原子的芳族、脂族、芳脂族或脂环族基团,其中的一个或多个C原子可用F、Cl、Br或I代替,y可设定为0-6的数值。优选的基团L是五氟苯基、四氟苯基、三氟苯基、氟苯基、苯基、4-三氟甲基苯基、3,5-双(三氟甲基)苯基、2,4,6-三(三氟甲基)苯基、氟和碘。特别优选的阴离子Y-是PF6 -、SbF6 -和B(C6F5)4 -。其它的二芳基碘鎓化合物,例如公开在US-A-4246703中。
特别合适的二芳基碘鎓化合物是:●四氟硼酸二苯基碘鎓●六氟磷酸二苯基碘鎓●六氟锑酸二苯基碘鎓●四(五氟苯基)硼酸二苯基碘鎓●六氟磷酸双-(4-甲基苯基)碘鎓●六氟锑酸双-(4-甲基苯基)碘鎓●四(五氟苯基)硼酸双-(4-甲基苯基)碘鎓●六氟磷酸苯基-4-甲基苯基碘鎓●六氟锑酸苯基-4-甲基苯基碘鎓●四(五氟苯基)硼酸苯基-4-甲基苯基碘鎓●六氟锑酸苯基-4-甲氧基苯基碘鎓●四(五氟苯基)硼酸苯基-4-甲氧基苯基碘鎓●六氟苯基锑酸苯基-3-硝基苯基碘鎓●四(五氟苯基)硼酸苯基-3-硝基苯基碘鎓●六氟锑酸双(4-叔丁基苯基)碘鎓●四(五氟苯基)硼酸双(4-叔丁基苯基)碘鎓●六氟锑酸苯基-4-二苯基碘鎓●六氟磷酸二萘基碘鎓●六氟锑酸二萘基碘鎓●四(五氟苯基)硼酸二萘基碘鎓●六氟锑酸双(4-十二烷基苯基)碘鎓●四(五氟苯基)硼酸双(4-十二烷基苯基)碘鎓●六氟锑酸-4-甲基苯基-4-异丙基苯基碘鎓●四(五氟苯基)硼酸-4-甲基苯基-4-异丙基苯基碘鎓
成分b)的α-二羰基化合物指的是具有以下结构的化合物:其中R4和R5相同或不同,并且可以是取代的或未取代的脂族或芳族基团。R4和R5可一起构成环状结构,该环状结构是未取代的或被脂族、脂环族、芳族、杂芳族或稠合芳族基团所取代。优选的α-二羰基化合物是樟脑醌、苯偶酰、2,3-丁二酮和3,3,6,6-四甲基环己二酮,樟脑醌是特别优选的。
成分c)的可阳离子固化的化合物指的是具有以下结构的脂族或芳族环氧化物(类型1)、脂环族环氧化物(类型2)或氧杂环丁烷(类型3):
类型1 类型2 类型3其中的符号代表:R10具有0-22个、优选0-18个C原子的脂族、脂环族或芳族基团或这些基团的结合体,其中的一个或多个C原子可以用O、C=O、-O(C=O)-、SiR3和/或NR2代替,其中R是具有1-7个C原子的脂族基,其中的一个或多个C原子可以用O、C=O和/或-O(C=O)-代替,R11具有1-18个、优选1-15个C原子的脂族、脂环族或芳族基团或这些基团的结合体,其中的一个或多个C原子可以用O、C=O、-O(C=O)-、SiR3和/或NR2代替,其中R是具有1-7个C原子的脂族基,其中的一个或多个C原子可以用O、C=O和/或-O(C=O)-代替,R12、R13、R14、R15互相独立地为H原子或具有1-9个、优选1-7个C原子的脂族基,其中的一个或多个C原子可以用O、C=O、-O(C=O)-、SiR3和/或NR2代替,其中R是具有1-7个C原子的脂族基,其中的一个或多个C原子可以用O、C=O和/或-O(C=O)-代替,n 2-7,优选为2-5,尤其是2-4,m 1-10,优选为1-7,尤其是1-5,p 1-5,优选为1-4,尤其是1或2,q 1-5,优选为1-4,尤其是1或2
特别合适的成分c)的环氧化物和氧杂环丁烷是●四(2,1-乙二基-3,4-环氧环己基)-1,3,5,7-四甲基环四硅氧烷,●1,10-癸二基双(氧亚甲基)双(3-乙基氧杂环丁烷),●1,3,5,7,9-五(2,1-乙二基-3,4-环氧环己基)-1,3,5,7,9-五甲基环五硅氧烷,●氧化乙烯基环己烯,●二氧化乙烯基环己烯,●3,4-环氧-6-甲基环己烯羧酸3,4-环氧-6-甲基环己基甲基酯,●双(2,3-环氧环戊基)醚,●己二酸3,4-环氧-6-甲基环己基甲基酯,●3,4-环氧环己基-5,5-螺-3,4-环氧环己烷间二噁烷,●1,4-丁二基-双氧亚甲基双(3-乙基氧杂环丁烷),●3,4-环氧环己烷羧酸3,4-环氧环己基甲基酯,●1,1,3,3-四甲基-1,3-双(2,1-乙二基-3,4-环氧环己基)二硅氧烷,●己二酸双-(3,4-环氧环己基甲基)酯
成分d)的填料可以是通常的牙科填料,例如石英、磨碎的任选地为不透X射线的或反应性的玻璃、碎片聚合物、微溶的氟化物如CaF2、YF3(EP-B-0238025)、硅胶和热解的硅酸或其颗粒。
该组合物也可以含有一种或多种通式为AnMFm的水溶性无机复合氟化物作为提供氟的成分,其中A代表单价或多价阳离子,M代表Ⅱ、Ⅲ、Ⅳ或Ⅴ主族或副族的金属,n代表1-3的整数,m代表3-6的整数(DE-A-4445266)。
为了较好地掺入到聚合物基质中,有益的是可以使填料和(如果合适)不透X射线的添加剂如YF3疏水化。通常的疏水剂是硅烷,例如缩水甘油氧丙基三甲氧基硅烷。无机填料的最大粒径优选为20μm,尤其是12μm。特别优选采用平均粒径小于7μm的填料。
具有氧化作用的成分d)的添加剂可以是有机或无机的固体或液体。这些添加剂促进了引发并增加了聚合度。合适的具有氧化作用的添加剂是氢过氧化物如氢过氧化枯烯,二烷基过氧化物如过氧化二叔丁基,二芳基过氧化物如过氧化二苯甲酰,过酸酯如过苯甲酸叔丁酯或异壬酸叔丁酯,或是无机氧化剂如过硫酸钾或过硼酸钠,特别优选的是氢过氧化枯烯或过硫酸钾。
成分e)的芳族胺指的是具有以下结构的化合物:其中R6、R7和R8相同或不同,且互相独立地代表H原子、具有1-19个、优选1-7个C原子的脂族、芳族或芳脂族基,其中的一个或多个C原子可以用O、C=O、-O(C=O)-、SiR9 3和/或NR9 2代替,其中R9是具有1-7个C原子的脂族基,其中的一个或多个C原子可以用O、C=O和/或-O(C=O)-代替,z可设定为1-5的数值。R6与R7和/或R6与R8可以一起形成环状结构,该环状结构是未取代的或被脂族、脂环族、芳族、杂芳族或稠合芳族基团所取代。
优选的胺是二甲基苯胺、二乙基苯胺、4-二甲基-氨基苯甲酸乙基酯、4-二甲基氨基苯甲酸2-丁氧基乙基酯、4-二甲基氨基苯甲酸2-乙基己基酯、4-二甲基氨基苯甲醛和它们的衍生物如苯甲醛肟、偶氮甲碱化合物、亚苄基苯胺、三苯甲醛缩二胺、苯偶姻、苯偶酰、氢化苯偶姻和苯甲酸苄基酯。
本发明的组合物通过将各种成分混合在一起而制成。添加顺序不是关键性的。优选的是,首先将含有环氧基和/或氧杂环丁烷基的化合物加入到混合容器中,并将二芳基碘鎓化合物、α-二羰基化合物和芳族胺搅拌加入其中。然后混入填料和其它改性剂。
本发明的组合物适合于基于含有环氧基和/或氧杂环丁烷基的化合物的光致阳离子聚合。引发剂体系适合于固化带有填料成分的组合物。该组合物为补牙用途提供了特殊的优点。该可聚合配料出乎意料地具有短固化时间,固化时间可以根据附加活化剂(例如具有氧化作用的添加剂)的性质和浓度非常准确地进行调节。
本发明的组合物适合于胶合、灌封和涂覆基材以及用作补牙组合物。
本发明组合物的一个非常显著的优点是固化的组合物具有特别良好的美学效果。聚合物可以根据牙齿的颜色进行配制,其结果特别适合于补牙的用途。由于聚合物具有高透光度,因此达到了特别深度的固化。
本发明将通过以下实施例进一步说明:
实施例
通过混合表1中所述的化合物,制备实施例1-13的不含填料成分的可阳离子固化的单组分组合物。这些组合物是用于由其制备的实施例14-20(表2)的带有填料成分的组合物(复合物)的树脂基质。
表1不含填料成分的可阳离子固化的单组分组合物的成分
实施例(wt.%) | ||||||||||||||
成分 | 化合物 | 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | 10 | 11 | 12 | 13 |
a) | 六氟锑酸双-(4-十二烷基苯基)碘鎓 | 1.05 | 0.6 | 2.0 | 1.0 | 2.0 | 1.2 | 2.1 | 2.0 | |||||
a) | 四(五氟苯基)硼酸-4-甲基苯基-4-异丙基苯基-碘鎓 | 1.4 | 1.2 | 2.0 | 2.0 | 1.0 | 2.1 | 2.1 | ||||||
b) | 樟脑醌 | 1.05 | 1.4 | 0.6 | 0.9 | 0.5 | 0.4 | 0.4 | 0.8 | 0.6 | 0.85 | 0.895 | 0.89 | 1.0 |
e) | 4-二甲基氨基苯甲酸乙酯 | 0.9 | 0.6 | 0.3 | 0.1 | 0.2 | 0.2 | 0.05 | 0.005 | 0.005 | ||||
e) | 4-二甲基氨基苯甲酸2-丁氧基乙基酯 | 0.1 | 0.4 | 0.2 | 0.3 | 0.005 | 0.3 | |||||||
c) | 3,4-环氧环己烷羧酸3,4-环氧环己基甲基酯 | 80.0 | 50.0 | 48.0 | 97.0 | 48.5 | 48.5 | 30.0 | 48.5 | 48.7 | ||||
c) | 己二酸双-(3,4-环氧环己基甲基)酯 | 17.0 | 33.0 | 48.7 | 48.3 | 30.0 | ||||||||
c) | 1,3,5,7-四(2,1-乙二基-3,4-环氧环己基)-1,3,5,7-四甲基环四硅氧烷 | 46.0 | 49.0 | 64.0 | 48.7 | 48.4 | 48.5 | 27.0 | 48.5 | 48 | ||||
c) | 3,3′-(1,10-癸二基双(氧亚甲基))双(3-乙基氧杂环丁烷) | 97.0 | 48.5 | |||||||||||
d) | 氢过氧化枯烯/在枯烯中的80%溶液 | 1.1 | 1.2 | |||||||||||
d) | K2S2O8 | 0.9 | ||||||||||||
d) | 过苯甲酸叔丁酯 | 0.5 |
当用产生波长范围为400-500nm的可见光的灯(照明设备EliparⅡ,ESPE Dental-Medizin GmbH&Co.KG Germany)照射时,实施例1-13的所有组合物在20秒内固化。所得聚合物透明并具有高强度。
当用上述灯照射时,表2所表征的实施例14-20的复合组合物在40秒内固化。
表2带有填料成分的可阳离子固化的单组分配方的组合物
a)硅烷化的研磨石英粉,Quarzwerke Frechenb)石英,平均粒径为0.9μm,用5%的缩水甘油氧丙基三甲氧基硅烷硅烷化c)该碎片聚合物是通过研磨和筛分固化的实施例7组合物得到的。
实施例号 | 不含填料成分的组合物 | 填料 | |||
组合物的相应实施例号 | wt.% | Silbond 800ESTa)wt.% | 石英b)wt.% | 碎片聚合物c)wt.% | |
14 | 6 | 30 | 70 | ||
15 | 7 | 22 | 78 | ||
16 | 11 | 40 | 60 | ||
17 | 12 | 27 | 73 | ||
18 | 12 | 25 | 75 | ||
19 | 12 | 40 | 60 | ||
20 | 13 | 29 | 71 |
所得聚合物是无色到牙齿颜色的。
表3包含了采用实施例14-20的复合组合物得到的基本性能的测定结果。
表3固化的实施例14-20组合物的性能
实施例 | 抗弯强度ISO 4049 | 抗压强度 |
14 | 110 MPa | 381 MPa |
15 | 131 MPa | 410 MPa |
16 | 95 MPa | 352 MPa |
17 | 99 MPa | 361 MPa |
18 | 122 MPa | 395 MPa |
19 | 75 MPa | 297 MPa |
20 | 113 MPa | 356 MPa |
这些实施例说明,由于固化的组合物仅有浅的固有色以及非常好的机械性能,因而特别适合于补牙的应用,尤其是作为填充材料和固定胶,这点可由本发明的组合物达到。
Claims (14)
1、用可见光可阳离子固化的组合物,含有:
(a)0.01-8wt.%的至少一种二芳基碘鎓化合物,
(b)0.01-8wt.%的至少一种α-二羰基化合物,
(c)10.0-99.9wt.%的至少一种含环氧基和/或氧杂环丁烷基的化合物,
(d)0-85wt%的改性剂,如填料、染料、颜料、流动改进剂、触变剂、聚合增稠剂、具有氧化作用的添加剂、稳定剂和阻聚剂,
其特征在于组合物还含有
(e)0.001-5wt.%的至少一种芳族胺。
2、权利要求1的组合物,其特征在于该组合物所合成分的量如下:
(a)含量为0.1-5wt.%
(b)含量为0.1-5wt.%,以及
(e)含量为0.01-3wt.%。
3、权利要求1的组合物,其特征在于成分(a)的二芳基碘鎓化合物具有以下结构:
[((R1)aAr1)-I-(Ar2(R2)b)]+Y-其中各符号代表:
Ar1和Ar2互相独立地为不同的取代或未取代的、稠合或非稠合的具有4-20个C原子的芳族体系,优选为苯基、甲苯基、枯基、茴香基、氯苯基、硝基苯基、萘基、噻吩基、呋喃基和吡唑基,
R1和R2互相独立地为H原子、具有1-19个、优选1-9个C原子的脂族基,其中的一个或多个C原子可以用O、C=O、-O(C=O)-、F、Cl、Br、SiR3 3和/或NR3 2代替,其中R3是具有1-7个C原子的脂族基,其中的一个或多个C原子可以用O、C=O和/或-O(C=O)-代替,其中芳族体系Ar1和Ar2可以通过R1和/或R2互相连接,
a和b互相独立地为1-5的整数,以及
Y是下式的低亲核性阴离子:
KxLy -其中各符号代表:
K第Ⅲ、Ⅴ或Ⅶ主族的元素,优选为B、Al、P、Sb、As或I,
x 1-4的数,
L互相独立地为具有1-25个C原子的芳族、脂族、芳脂族或脂环族基团,其中的一个或多个C原子可用F、Cl、Br或I代替,以及
y 0-6的数。
4、权利要求3的组合物,其特征在于Y-是PF6 -、SbF6 -或B(C5F5)4 -。
6、权利要求5的组合物,其特征在于作为成分(b),该组合物含有樟脑醌、苯偶酰、2,3-丁二酮和/或3,3,6,6-四甲基环己二酮,优选的是樟脑醌。
8、权利要求7的组合物,其特征在于作为成分(c),该组合物含有二甲基苯胺、二乙基苯胺、4-二甲基-氨基苯甲酸乙酯、4-二甲基氨基苯甲酸2-丁氧基乙基酯、4-二甲基氨基苯甲酸2-乙基己基酯、4-二甲基氨基苯甲醛、苯甲醛肟、偶氮甲碱化合物、亚苄基苯胺、三苯甲醛缩二胺、苯偶姻、苯偶酰、氢化苯偶姻和/或苯甲酸苄基酯,优选的是4-二甲基-氨基苯甲酸乙酯、4-二甲基氨基苯甲酸2-丁氧基乙基酯或4-二甲基氨基苯甲酸2-乙基己基酯。
9、权利要求1-8的组合物,其特征在于成分(c)的含有环氧基和/或氧杂环丁烷基的化合物具有以下结构:
R10具有0-22个、优选0-18个C原子的脂族、脂环族或芳族基团或这些基团的结合体,其中的一个或多个C原子可以用O、C=O、-O(C=O)-、SiR3和/或NR2代替,其中R是具有1-7个C原子的脂族基,其中的一个或多个C原子可以用O、C=O和/或-O(C=O)-代替,
R11具有1-18个、优选1-15个C原子的脂族、脂环族或芳族基团或这些基团的结合体,其中的一个或多个C原子可以用O、C=O、-O(C=O)-、SiR3和/或NR2代替,其中R是具有1-7个C原子的脂族基,其中的一个或多个C原子可以用O、C=O和/或-O(C=O)-代替,
R12、R13、R14、R15互相独立地为H原子或具有1-9个、优选1-7个C原子的脂族基,其中的一个或多个C原子可以用O、C=O、-O(C=O)-、SiR3和/或NR2代替,其中R是具有1-7个C原子的脂族基,其中的一个或多个C原子可以用O、C=O和/或-O(C=O)-代替,
n 2-7,优选为2-5,尤其是2-4,
m 1-10,优选为1-7,尤其是1-5,
p 1-5,优选为1-4,尤其是1或2,
q 1-5,优选为1-4,尤其是1或2。
10、权利要求9的组合物,其特征在于作为成分(c),该组合物含有
1,3,5,7-四-(2,1-乙二基-3,4-环氧环己基)-1,3,5,7-四甲基环四硅氧烷、1,10-癸二基双(氧亚甲基)双(3-乙基氧杂环丁烷)、1,3,5,7,9-五(2,1-乙二基-3,4-环氧环己基)-1,3,5,7,9-五甲基环五硅氧烷、氧化乙烯基环己烯、二氧化乙烯基环己烯、3,4-环氧-6-甲基环己烯羧酸3,4-环氧-6-甲基环己基甲基酯、双(2,3-环氧环戊基)醚、己二酸3,4-环氧-6-甲基环己基甲基酯、3,4-环氧环己基-5,5-螺-3,4-环氧(环己烷间二噁烷)、1,4-丁二基-双(氧亚甲基)-双-(3-乙基氧杂环丁烷)、3,4-环氧环己烷羧酸3,4-环氧环己基甲基酯、1,1,3,3-四甲基-1,3-双(2,1-乙二基-3,4-环氧环己基)二硅氧烷和/或己二酸双-(3,4-环氧环己基甲基)酯。
11、权利要求1-10的组合物,其特征在于作为成分(d)的具有氧化作用的添加剂,该组合物含有氢过氧化枯烯、过氧化二叔丁基、二芳基过氧化物、过氧化二苯甲酰、过苯甲酸叔丁酯、异壬酸叔丁酯、过硫酸钾和/或过硼酸钠。
12、权利要求1-10的组合物,其特征在于作为成分(d)的填料,该组合物含有石英、磨碎的任选地为不透X射线的或反应性的玻璃、碎片聚合物、微溶的氟化物如CaF2、YF3、硅胶和/或热解的硅酸或其颗粒。
13、权利要求1-12的组合物用于胶合、灌封和涂覆基材的用途。
14、权利要求1-12的组合物用于补牙组合物的用途,尤其是用于制备补牙填充材料、粘结材料、填充胶和固定胶、作为临时修补物的塑料、表层材料、密封材料、假牙和作为生产全部或部分修补物的塑料。
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- 1998-08-19 AU AU80838/98A patent/AU753636B2/en not_active Ceased
- 1998-08-20 CN CNB981174876A patent/CN1173684C/zh not_active Expired - Fee Related
- 1998-08-21 DE DE59812289T patent/DE59812289D1/de not_active Expired - Lifetime
- 1998-08-21 CA CA002245548A patent/CA2245548C/en not_active Expired - Fee Related
- 1998-08-21 US US09/138,281 patent/US6084004A/en not_active Expired - Lifetime
- 1998-08-21 AT AT98115822T patent/ATE283021T1/de not_active IP Right Cessation
- 1998-08-21 EP EP98115822A patent/EP0897710B1/de not_active Expired - Lifetime
Cited By (4)
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CN100473681C (zh) * | 2000-02-18 | 2009-04-01 | 罗狄亚化学公司 | 用具有反应性功能的可聚合和/或可交联有机组合物处理塑料材料表面 |
CN100454142C (zh) * | 2000-03-29 | 2009-01-21 | 学校法人神奈川大学 | 光固化性和热固化性树脂组合物、其感光性干薄膜及使用其的图案形成方法 |
CN108350151A (zh) * | 2015-09-02 | 2018-07-31 | 维也纳科技大学 | 新的引发剂及其用于阳离子光聚合的用途 |
CN110317513A (zh) * | 2018-03-28 | 2019-10-11 | 常州格林感光新材料有限公司 | 用于金属表面腐蚀防护处理的光固化组合物、其应用及金属表面腐蚀防护处理的方法 |
Also Published As
Publication number | Publication date |
---|---|
AU753636B2 (en) | 2002-10-24 |
US6084004A (en) | 2000-07-04 |
JPH11130945A (ja) | 1999-05-18 |
EP0897710A2 (de) | 1999-02-24 |
CA2245548A1 (en) | 1999-02-21 |
DE59812289D1 (de) | 2004-12-30 |
CA2245548C (en) | 2009-06-09 |
EP0897710A3 (de) | 2000-09-06 |
CN1173684C (zh) | 2004-11-03 |
AU8083898A (en) | 1999-03-04 |
DE19736471A1 (de) | 1999-02-25 |
EP0897710B1 (de) | 2004-11-24 |
ATE283021T1 (de) | 2004-12-15 |
JP4344026B2 (ja) | 2009-10-14 |
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